


For You I Would

by cellar_light



Category: Supernatural
Genre: Alternate Universe, Anal Sex, Bottom Castiel (Supernatural), Dirty Talk, Emotional Manipulation, Established Castiel/Dean Winchester, First Time, Loss of Virginity, M/M, Mildly Dubious Consent, Rimming, Top Dean Winchester, Underage Sex, Virgin Castiel (Supernatural)
Language: English
Status: Completed
Published: 2020-05-21
Updated: 2020-05-23
Packaged: 2021-03-02 01:06:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 9,446
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23786794
Author URL: https://archiveofourown.org/users/cellar_light/pseuds/cellar_light
Summary: Castiel is pressured into having sex for the first time by his boyfriend. After saying 'no' to Dean's advances for a few months, he finally caves in.
Relationships: Castiel/Dean Winchester
Comments: 13
Kudos: 64





	1. Chapter 1

**Notes for the Chapter:**

> I'm currently working on transferring my fills to AO3. This one was originally posted [here](https://spnkink-meme.livejournal.com/76569.html?thread=27407385#t27407385) with the original prompt, though I have since then revised it somewhat.
> 
> Please read the tags carefully.  
> For a few words of caution that also includes spoilers, hover **THIS.**

"Don't you want to make me happy?"

Dean's voice was so soft, so small, when he asked the usual question after around fifteen minutes of making out lazily on the ragged old couch in his basement-bedroom and his hands were snaked under Castiel's shirt.

He was kind of being an asshole, Castiel knew that Dean must be aware about that, of how he was pressuring and guilt-tripping Castiel into sleeping with him, but they had been going out for quite a long time now, and Dean had been getting more and more desperate. His lips and the hands on Castiel's body didn't exactly make his position any easier, where he was, cornered against the cushions.

"Of course I do," Castiel mumbled as he wriggled a little under Dean's body, shifting against the soft cushioning. He wanted to get some space between them, but the look Dean gave him made him wonder if he seemed uncomfortable. "But do I have to have sex with you to achieve that?"

Dean sighed and started moving himself off Castiel until he was sitting on the other end of the couch. He ran a hand through his hair and Castiel caught him glancing when he was pulling his shirt back down over his stomach, a frown tight between Dean's brows.

"Look, Cas... I'm a senior now. We're together, yeah? But a guy my age, with a history like mine; we have needs, okay?" He said with a bit of a huff. "Someday you'll understand that too, and you'll regret being such a fucking prude and causing me all this pain."

Castiel sat up too and pulled his legs close to his chest. He looked at the floor and rested his chin against his knees. He wasn't a prude, not _that_ much of one anyway. He had known Dean for years, but they had only started dating a couple of months ago. Castiel had always looked up to him, envied and idolized Dean when he was younger, Dean was so tough and confident, going out with girls and sneaking beers from the grown-ups. He hadn't realized that he was _jealous_ until puberty hit, which was coincidentally also when Dean jokingly started teasing and hitting on him. Playful slaps on his ass, winks when no one was around and obscene whispers, all soon turned into something else, like a silent competition that none of them won.

Sometimes, Castiel wondered if the game was still going on, and if Dean wanted to get into his pants so badly only to win. Just so he could stick his tongue out later and brag about how he totally got him fooled, and then never shut up about how he won their little game.

But Dean wasn't fifteen anymore, and he probably didn't even remember the game. He seemed genuinely in love with Castiel, most of the time anyway, it was only lately that he had seemed to distance himself somewhat, spending more time with people his own age, going to parties and talking about college and girls, and he even watched porn in bed once while Castiel was sleeping over at his place. Despite the low volume, of course Castiel had woken up and realized what was going on when he heard soft moans from the laptop speakers and the rustling going on under the sheets on Dean's side of the bed. He had pretended to be asleep for both their sakes.

"You didn't swallow your tongue or something, did you?" Dean's voice was closer now, and he bumped his shoulder against Castiel.

"Hm? Oh," Castiel shook his head and blinked a few times, ridding himself of his thoughts and turned his attention back to Dean who had moved closer to him on the couch. "No, I just... I'm not certain that I'm ready, Dean."

Castiel didn't dare to look at Dean, he kept his eyes on the floor and chewed on the inside of his bottom lip, feeling like maybe he wasn't good enough for Dean. He was fifteen, only a sophomore, and he didn't experience the same kind of sex drive as Dean, not yet anyway. To him, losing his virginity was a big deal, and although he knew that Dean was the right person for that, because he loved and trusted him and it _felt_ right – the moment wasn't there yet. Plus, mentally, he wasn't sure that he feel prepared or ready enough.

Sometimes, it seemed like Dean liked him less because of it. It was a constant worry in the back of his mind that Dean would leave him for someone else, someone who would actually sleep with him.

"It doesn't mean that I don't like you," Castiel mumbled and turned his head to look at Dean.

"I know, Cas... But we're in this together. Your decision affects me."

"What you said before..." Castiel started tentatively, pausing to let go of his legs and let his feet down on the floor again. "Do I really cause you pain?" His voice was barely just a whisper, and he couldn't keep his hands still. He didn't want to hurt Dean, intentionally or not.

Dean opened his mouth but closed it just as fast, as if he was hesitating. A moment, and then he shrugged and threw his arm around Castiel's shoulders. Castiel was pulled in close to Dean and almost instinctively placed his head against his shoulder.

"Yeah...," Dean said, somewhat trembling. "I like you, Cas, a lot. You're hot, and you turn me on and I love you and I want to share... that intimate moment with you. Can't you at least just give me a hand, every once in a while?"

They were both quiet for a moment. Dean ran his fingers through Castiel's hair, and Castiel pondered and tried to process everything. They had played with each other before, it wasn't like he was clueless when it came to sex, although they mostly just rutted against each other or Dean had a hand between them when they were making out. Truthfully, he wanted to sleep with Dean, just not yet. He wanted to wait and he wanted Dean to respect that and let him take his time. He wanted to move slow and let his courage and confidence build up some more first. He only needed to come up with the right way to phrase all that into a sentence that wouldn't scare Dean off.

Dean broke the silence first.

"You know, I've thought about applying to college. Get the hell out of this piece of shit town for a couple of years. I wanna make sure you're worth waiting for."

Castiel frowned at that and looked up. "What's that supposed to mean?"

He couldn't help but feel offended. He had sort of figured out that they wouldn't stick together forever, especially with the different stages of life they were in, but whether or not he was _worth_ it was a whole other thing.

Dean rolled his eyes and placed his hands on Castiel's chest and gently pushed him onto his back again, crawling on top of him easily. He looked deep into Castiel's eyes and pressed a soft kiss to the corner of his mouth.

"Don't worry, babe, you've got it all twisted up inside that brilliant brain of yours," Dean murmured and kissed his cheek. "I wanna get a taste of you before I leave, that's all. Get you nice and ready so we can keep in touch while I'm a couple of states over."

"Keep in touch?"

"Phone sex, Cas. Webcam shenanigans, the whole package deal of long-distance relationships."

"Oh."

Castiel hadn't thought about that, and when he imagined himself sitting in his bed with his laptop, hand down his pants while Dean was watching on the other side of the screen and doing the same to himself, he couldn't help but blush.

"Like I said. I've got needs. I'm sure there's plenty of nice ladies and cute guys at college who'd wait in line to get a chance to hop on the Winchester Ride," Dean said with a crooked smirk and a wink before he continued placing a trail of kisses down Castiel's jaw and neck.

Castiel rolled his eyes. "Don't flatter yourself," he grumbled, but Dean's words still echoed inside of his head. He was a sophomore, nothing but a kid really, at least compared to Dean who was already busy planning on going to _college_ , to meet new people to party with and fuck, and he'd probably forget that Castiel even existed as soon as he left Kansas. 

There was a moment then, when everything felt like it was frozen in time, that brought Castiel out of his thoughts. Dean was moving so slowly and the basement was unbelievably silent. The only thing that was rushing was the blood inside Castiel's body, downwards, and around, and he couldn't help the way his hormones and body reacted when Dean was rutting and rubbing up against him all over. It made him dizzy, and everything was so familiar.

"Don't you want to make me happy?"

What if Dean moved and moved on, what if Dean forgot all about him and his opportunity was lost? Maybe there wasn't such a thing as a perfect, or even special, opportunity? If he didn't lose his virginity to Dean, then who knew how long it would take, if it _ever_ would happen to him?

And then reality dropped out of nowhere and things were happening fast again. Crashing, spinning.

Too fast.

"Okay."

**Notes for the Chapter:**

> This story has three parts. The next chapter will be posted tomorrow, and then the last part the day after that!


	2. Chapter 2

Castiel would never have thought that such a tiny little word could have such a huge impact, such enormous effects.

Dean's hands were snuggled under his shirt again, the fabric of it pushed up against his armpits, when Castiel mumbled the tiny little word of consent. From then on, he was extremely aware of how Dean had stopped everything that he was doing. Dean wasn't sucking hickeys onto his ribs anymore, and if it wasn't for the way Castiel could still feel Dean's breath against his slightly wet skin, he would have thought that the world really had stopped this time, or that Dean had suffered a stroke or something.

"What?" Dean's voice was quiet, wavering almost, as if he couldn't believe what he was hearing and had to double check. 

Lifting his head up, Castiel searched Dean's face for a moment before their eyes met. "Okay. I said okay. I want to make you happy. Would you let me?"

Castiel's hands were shaking, and Dean seemed to have noticed that too because he moved his own from Castiel's chest and laced their fingers together as he propped himself up on his elbows and grinned down at him.

"Really? Wow, Cas, look at you," Dean chuckled before he leaned down to lick his way into Castiel's mouth, continuing their make-out session from where they broke it off before. This time though, it was more heated, Dean especially seemed to give it his best. He had always been a great kisser, but this was exceptional.

His lips were soft as they captured Castiel's with perfected practice, sucking in his bottom lip and darting his tongue out to run it along the opening of his mouth. He teased his lips, pulled away to peck his nose once before coming down to kiss him deeply again, exploring his mouth as if this kiss was their very first.

The couch seemed to devour Castiel's frame as Dean put all his weight down on him while the kissing continued. It made him feel a little stuck, closed in between Dean's firm chest and the cushions, but he wasn't about to complain. He liked it, it felt hot, and he liked kissing Dean. It was what happened with Dean when they were kissing that he didn't like, how it always riled him up and made him expect more. But this time, he had agreed to give Dean whatever he wanted, so there was no backing out now.

"God, you taste fucking amazing." Dean groaned when he pulled away. His cheeks were flushed, green eyes droopy and lust filled. His plump lips were red, kissed swollen and Castiel knew he probably looked the same.

Dean held himself up on his hands and moved his leg between Castiel's, pressing his knee up against his crotch and his growing erection. It was fascinating yet terrifying how Dean could become so different in a matter of seconds. He seemed so... confident, so grown up. It wasn't the immature, silly boy Castiel used to hang out and make out with. Dean like this was beautiful, hot even, and he was still _Dean,_ and Castiel was intrigued to get to know this side too.

Then Dean bent down again, pushed his hips forward over Castiel's thigh and he could feel the outline of Dean's dick against his leg. He could feel the heat surging from that area, and it went straight to his groin. Part of him wished that it hadn't. Dean was breathing heavily now, and the way he moved reminded Castiel of an animal that had locked onto a prey, determined to get what it wanted, hot-blooded and eager.

Dean moved a hand up to his hair. He tugged Castiel's head to the side and kissed him hard, bit gently on his lips and moaned into his mouth. The way he kissed wasn't as delicate and perfect as before, but pleasurable nonetheless. Open-mouthed and sloppy, without much finesse.

This time, Castiel was the one who moaned, and he was so surprised himself, that he stopped everything for a second to stare at Dean in shock.

"Fuck, Cas. That's so hot," Dean said in response, and the hand that wasn't carding through Castiel's sweaty hair and pulling, gently bending his neck backwards to allow him to bite and suck over Castiel's neck, moved down between their bodies, and palmed over his cock.

From there on, things happened faster than Castiel could react. His shirt was off, which he didn't notice until Dean took one of his nipples between his teeth. Dean wasn't wearing a shirt anymore either, and when Castiel looked toward the growing pile of clothes on the floor next to the couch, he saw that Dean's jeans were also apparently off. He decided that it wasn't worth thinking about how exactly he hadn't paid attention to any of this happening, or the fact that Dean's hands were busy trying to pull _his_ pants down. Instead, he lifted his hips up to allow Dean to get them off all the way, and when all the too many layers of clothing were removed from between them, and their dicks were only separated by their boxers, Castiel started freaking out.

Calming kisses or hand holding didn't help this time, so Dean pulled Castiel up from the couch and pushed him towards the bathroom. "Go take a hot shower, you'll relax in no time, babe." He shot Castiel a wink and pointed at him with his fingers shaped like a gun. "Don't jerk off!"

~ ~ ~

Showering helped somewhat, but Castiel's heart was still beating heavily inside his chest, drumming against his rib cage so hard that it was a wonder that the sound didn't echo throughout the basement. He soaped himself up quickly, trying to be as thorough as possible without thinking too much of what was to come. The shower was supposed to relax him, after all.

Dean was still sitting on the couch, waiting, boxers tight over his erection when Castiel walked out of the bathroom, towel wrapped around his hips. His hair was still a little damp and left a trail of water that dripped behind his heels when he walked over towards the couch. The air in the basement was moist, heavy and hard to breathe and Castiel wasn't so sure that this was a good idea anymore.

As he came closer, Dean stood up and smiled brightly at him. "Look at you," he said and raked his eyes over Castiel's body.

"Dean–," Castiel started, ready to tell him that he didn't want to anymore, ready to apologize for leading him on for this long, ready to take all of Dean's disappointment and anger. They might as well break up right then and there, Castiel thought, because what was the point of going through all of this confusion?

"I know, baby," Dean cut him off and pulled him in by his wrist and held him close to his chest. "I'll make it good, okay? Promise, I'll make you feel so good."

Everything he had prepared to say seemed to leave his mind as he deflated, speechlessly lost in the glittery green of Dean's sparkling eyes.

He let out a sigh, and closed his mouth again as Dean began to move him backwards towards the bed in the far corner of the basement, until the back of his knees collided with the mattress and Dean playfully pushed him onto his back.

Defiant butterflies flapped with their wings inside Castiel's stomach, making his heart flutter slightly as Dean crawled on top of him, his warmth enveloping Castiel's body, making his thoughts rush. Okay, perhaps this wouldn't be so bad, after all, Dean wasn't a bad guy, Castiel knew he could trust him to be careful. Besides, part of him _did_ want this, mostly the lower part of his body, but still.

"I wanna eat you out," Dean mumbled after a moment, mouth close against Castiel's neck, tongue licking over his skin gently. His hands were tugging at the towel around Castiel's waist, impatient to get it off. "You sure you wanna do this, Cas?"

Castiel swallowed, cheeks warm. "Yes," he said, nodding. It wasn't a lie. He did want to do this. If he was going to lose his virginity to anyone, it would be with Dean. Although, if Dean had asked him if he wanted to do this _now,_ his answer might have been different.

"You're doing great Cas," Dean said with a big grin on his lips as he leaned up on his elbows to kiss him gingerly. A breath, and then, "Want you to turn around for me, can you do that baby?"

Albeit a little nervous, Castiel did as he was told and turned around to lie on his stomach. He felt Dean place his hands on the back of his knees and urged his legs apart, pushed at them until Castiel complied and moved up on all fours. He could feel Dean's weight shift on the mattress as he moved in between his legs, hands rubbing over his thighs a couple of times before he pulled the towel off from around Castiel's hips and dropped it next to them on the bed. Castiel had never felt so exposed before, ass up in the air, so Dean could see everything. He felt like he was on a stage, and Dean was on front-row view. From the way his heart was beating, it was like he had just finished a marathon – and they hadn't even started doing anything yet.

"Wow, Cas..." Castiel could swear he heard Dean breathe out in something like awe from behind him. And then hands were grabbing his ass, massaging his ass cheeks and pulling them apart, perhaps a little too roughly. "God, why did we wait so long to do this?" Dean mumbled.

"I don't know..." Castiel said. He could feel the hot breath coming out of Dean's mouth hit his hole, his face probably just inches away from his ass, a strange sensation, yet still somehow exciting, and all kinds of wrong. Castiel fisted his hands in the sheet and closed his eyes, not even daring to imagine what to expect.

The first thing he noticed was Dean's nose against his ass, his thumbs still holding his cheeks apart. Then, there was the soft press of a wet tongue against his hole that made him gasp.

Dean chuckled, face buried against his ass, when Castiel tensed up again. "C'mon, relax. I'll go slow."

It was easier said than done. Castiel let out a shaky breath and then sucked it right back in as Dean began to lap eagerly over his hole. He hadn't been lying about going slow. Dean took his time as he teased the rim with his tongue until Castiel was feeling sloppy and wet all over and he couldn't help the way he pressed back closer when he felt Dean's tongue tense up deliciously, firm enough to want to feel the tip of it push past the ring of muscle around his hole. He'd never admit how much he liked the feeling of Dean getting his ass so nice and wet, but he assumed it must be obvious from the way he was panting into the pillow and the how heavy his dick was between his legs, body slowly melting closer down against the mattress to find friction and relaxation.

"Jesus Cas, you're so fucking delicious," Dean said breathily as he pulled away. "One day I'm gonna open you up on my tongue, just let you ride my face until you're dripping like a girl, would you like that baby?"

It was so dirty, Castiel just _'mm'd_ in response and nodded, still too much in shock to form coherent sentences, face warm from Dean's words.

Half a minute later, Dean shifted behind him. Castiel turned his face to the side and watched as Dean crawled to the nightstand where he grabbed a bottle of lube and a pack of condoms from the drawer. He turned his head back to the pillow then, ignoring the way his heart sped up at the sight of the items and the change of weight over the mattress as Dean climbed back to him until he was seated between his spread legs again. There was the sound of a bottle cap popping open, and then the slick gel drizzled between his ass. It was cold, but nice, and it warmed up once Dean started moving his fingers over his ass, rubbing the slick over his hole properly. It was a different feeling from Dean's tongue, firmer, but still nice nonetheless.

It was then, once the lube was warmed up against his skin while Dean's fingers rubbed over his hole, that Dean stopped, hand still nestled between the cleft of his ass. There was the tentative press of a finger, pushing gently at the rim like a button. Growing all the more cautious of what was about to happen, Castiel held his breath, and sure enough, Dean slowly eased the tip of his finger inside. On the small of his back, Dean's other hand was rubbing comforting circles, steadying him somewhat as he tried his best to get used to the intrusion for a moment before Dean began pushing his finger in more, all the way until Castiel could feel the rest of his knuckles prod against his ass when Dean couldn't get it any further inside.

"You're doing all right there, buddy?" Dean's voice was calm and collected, but strained as if he was clenching his jaw.

"Dean, don't call me 'buddy' in bed," Castiel hissed, face buried in his pillow while he tried not to focus on the strange feeling of Dean's finger inside his ass and the way it stretched him.

Dean laughed at that, warm and loving with his whole body, which made his hand shake and the finger in his hole moved slightly. "Sorry, angel," Dean corrected himself. "I'm gonna add another soon, okay?" He kept moving his hand, Castiel could feel it slide in and out of him, teasing at the rim and his insides.

He pressed his face further into the soft pillow and groaned. "Dean, I'm ready."

"You sure? We should probably take it slow."

He couldn't bear to tell Dean that he just wanted to get it over with, let him have his way with him to ensure that he wouldn't find someone more willing to let him get his dick wet. "Get on with it, Dean," Castiel said and nodded, face still pressed against the pillow.

"Okay, I guess. Just don't wanna hurt you..." Dean stopped moving his hand and seemed to be leaning over his back until he had moved on top of him. Dean pressed his mouth against the nape of Castiel's neck, silky soft lips meeting his skin. The movement seemed to make the finger still inside his hole press further, nudging against something that had him seeing stars and his body jerked as if being shocked by electricity.

"Ohh," Castiel gasped, eyes shooting open at the pleasurable sensation as white hot pleasure shot right to his dick for the split of a second. It was like a mini-orgasm, or the buildup of one, and he needed more.

Within seconds of his reaction, Dean was back between his legs, still working him open on his fingers. He added another one, just like he had said he would, and Castiel rolled his hips back to meet every thrust of his hand, hoping that maybe he would feel that sensation again, but also wanting to show Dean that he wanted this, that he wanted Dean to spread him open and get him ready for his cock.

When Dean inserted a third finger into him, Castiel thought for a moment that he was going to break, split in half on Dean's hand and paint the bed sheets with sin. He grimaced into the pillow, bit down hard on his lip to keep from whimpering. The nice sensation wasn't anywhere close... Wasn't this supposed to be pleasant? It hurt so much back there now, the sensation hadn't returned and he couldn't do anything about the way his hips and legs instinctively jerked away from the pain.

"I... I think that's enough," Dean mumbled, concern laced in his voice, and removed his fingers, leaving Castiel's hole exposed and puffy.

He sounded a bit disappointed, Castiel hoped he wasn't disappointed, hoped that Dean hadn't noticed him trying to move away from his hand. He didn't want to seem weak, what if Dean would stop now and move on from him? What was he good for if he couldn't have sex with Dean? If he couldn't even take his fingers and _like it?_

"Are you going to do it now? Put it in me?" Castiel asked shakily and raised his head up from the pillow to look over his shoulder at Dean. His voice was brittle, almost fragile and he was scared that he sounded a lot more worried than hopeful.

But to his surprise, Dean laughed, still warm and sweet. He rubbed a hand over Castiel's back in comfort. "Yeah, Cas," he said with a crooked smile and chuckled again. "I'd like to do that now, if you still want to."

They had already made it this far, Castiel thought, so they might as well continue and get it over with. It would be unnecessarily mean of him to pull out now and say that he wasn't up for it anymore, especially considering how hard he was, despite his conflicted mind, and Dean would probably get angry. He hadn't seemed disappointed that Castiel had pulled away from his hand though, quite the opposite actually, he was kind of sweet about it. That was the only thing that kept Castiel going right now, Dean wasn't being a jerk, he was talking to him with a soft voice, constantly keeping his hands on him as if to make sure that he was there and that he wasn't going to hurt him. He was laughing, not in a taunting way, and when Castiel looked at him again over his shoulder, Dean looked back at him like he was in love.

Perhaps he was making it all up in his head again. How bad could it be? They were in love, and people in love were supposed to sleep with each other, right? That was a part of keeping a healthy relationship. Dean had even given him an out, _'if you still want to'_.

"I'd like that," Castiel replied with a soft smile before he could change his mind.

Dean beamed at him, green eyes sparkling before he bent down to press a trail of kisses over the small of Castiel's back. It almost distracted him from the kind of wet sound of skin flapping against skin as Dean prepared himself with putting on the condom and more lube. Castiel closed his eyes. His own cock was long forgotten and neglected, jumping a little against his stomach when he once again was urged up on all fours and Dean moved in between his legs and his hands gripped around his hips.

"Tell me to stop babe, any time, just say the word and I'll stop."


	3. Chapter 3

"Tell me to stop babe, any time just say the word and I'll stop," Dean whispered.

Castiel could feel the slow, slick drag of Dean's erection between his cheeks and along the crack as Dean teased his ass with the length. Dean pulled back and pushed forward again, his cock sliding over Castiel's hole and back again. Gaining some momentum the next time he slid forward, the head of his cock pressed against Castiel's perineum for a moment, the sensation enough to cause an explosion of feelings to ripple through Castiel's body and he let out something reminiscent of a moan.

His face turned red at the sound of himself and the way Dean gripped his ass when he moaned. This was _hot --_ this he could live with. Dean could slide his thick cock against his ass until both of them came and Castiel would be okay with that. 

The heat spread from his face, down over his neck and back, and Dean seemed to have noticed from the way his breathing was getting harder, heavier. He pulled back from where his cock was comfortably seated against Castiel's ass one last time and then positioned his dick right in the middle, the head of it pressing impatiently against Castiel's hole.

Castiel swallowed as his thoughts stirred in the fog in his mind. Maybe he would like this too?

Dean curled his fingers over his hips and pushed forward slowly.

Castiel was silent. He held his breath, he was pretty sure anyway, as his mind went blank and he focused all of his energy to keep every muscle in his body relaxed. The feeling could only be described as intrusive. Thankfully, it didn't exactly hurt – not much anyway - but it wasn't comfortable either. Dean moved slowly, inching in little by little while the bed underneath their bodies creaked and groaned. It wasn't until Dean was seated all the way inside of him, his hips digging into the softness of his ass, that the silence between them was broken by Dean who let out a groan from the back of his throat. Castiel opened his eyes once and sucked in a breath of air and tried his best to stay calm, because every time he moved just a little, he could feel Dean's cock shift slightly inside of him.

"You okay?" Dean asked and rubbed his hands over Castiel's back again.

"I think so," Castiel replied, voice somewhat strained. His ass felt stretched, like it was tearing slightly, and although he could feel himself relaxing more and more around Dean, his body slowly adjusting to having him inside, he still didn't really like it much. Sweat pooled at the base of his neck. What if he moved too quickly and something _did_ tear? No. Dean would be kind to him. He took a breath. "It's strange," he added.

Dean's breathing was heavy behind him, and his hands felt a little rigid over his back, like he was holding himself back from moving. "Well, I think you feel fucking amazing, Cas," Dean murmured and then, confirming Castiel's suspicions, ever so slowly began to pull out.

A few moments later and Castiel could feel the head of Dean's cock catch at the rim, nearly slipping out of him. For a second his mind rushed with terror of Dean having to put it all the way back inside again if he pulled out completely, but his worry diminished when Dean stopped. Curious, Castiel looked back over his shoulder to find out why. Dean was grinning, looking down at the sight of their bodies being connected, a gorgeous spark in his eye and he was probably feeling like he'd climbed a mountain or something. Then, maybe with just a tiny bit too much excitement, Dean pushed himself back in.

Castiel groaned as his body was pushed up on the bed. His elbows wavered dangerously with the force of Dean's hips, but determined to not be a letdown, he moved his hips back to meet Dean's, even though it burned every time it pushed in deeper. He wanted to let the sounds growing in the back of his throat out, wanted to be loud and let Dean know how he felt, how big Dean's cock felt, and tell him all the things he guessed Dean wanted to hear. He wanted Dean to hear him whimper when he was buried all the way inside of him, Dean's pelvis against the back of his thighs, but he worried it would come out strained and like he was hurt. It was uncomfortable, sure, but not painful, just... not quite right either. He understood how it could be pleasurable, like before with the fingers. Perhaps their next times would have more potential...

"You're so tight, Cas, feel better than anyone," Dean whispered breathily. For some reason the words felt meaningless to Castiel, like he was just another notch in Dean's bedpost, another name on his list of triumphs, conquers.

Castiel clenched his jaw. He knew deep down that he was more than that. He was Dean's, and Dean was his. They were each other's, and what they had was special.

Dean eased his hips away, slipping out even further this time. Castiel ached with the loss of him, feeling empty and hollow and _raw_. Dean's hips snapped back, faster this time, making his body feel like it was burning. Dean pulled out and slammed back in again, and again, and each time it hurt a little less.

"Ohh," Castiel whimpered once he finally dared to, his eyes clenched as Dean hollowed him out and created a hole inside of him until all the pain was gone and all that was left was their bodies moving in bad rhythm. Sex wasn't what he had expected it to be. It was supposed to be special. But this was just... a cock, a part of somebody else inside of him. It should be a big deal, but it wasn't. He felt like Dean was peeling off layers of him, leaving him exposed and fragile, vulnerable.

Castiel breathed out harshly, turning his hands into fists in the sheets again as he buried his face into a pillow, trying not to cry as the emotions overcame him. He couldn't allow himself to be a baby about this. It meant a lot to Dean, so it meant a lot for him. He had to be a good boyfriend. He _loved_ him, after all.

Dean pushed back into him until he was balls deep. The sounds they made when their bodies were slammed together were filthy, just like in the porn Dean sometimes watched (but that usually involved a girl in some way, who always made the loudest, most silly sounds). Maybe Dean would appreciate it even more if he also made sounds like the girls in the videos? If he writhed and moaned and gasped loudly, blurted out immodest and obscene words back to him, perhaps it would be more enjoyable, for both of them? It didn't make any sense, and Castiel did not have it in him to even try it out, he was only thinking nonsense out of desperation at this point, or distraction, he guessed. Castiel bit his lip and opened his eyes, his gaze met the white of the sheets and the pillow that he was facing, insipid and unintelligible. There was no face there that he could read, no eyes he could find solace in.

"Jesus," Dean gasped on top of him. He leaned down and wrapped his arms around Castiel's waist and pressed kisses over his back. "Why'd we wait so long to do this again?" he blabbered, "I've jacked off so many times, wondering what your tight, pink hole would look like stretched around my dick."

"How romantic," the words left Castiel's mouth in a mumble before he could stop himself, his voice dripping with sarcasm.

Dean only laughed, warm as ever, and squeezed his waist one more time before he buried his face in the curve of his spine. "Oh come on, loosen up a little, Cas."

Fact was, he was loosening up. Little by little, Dean's cock sliding in and out of his ass nearly didn't hurt at all now. There was just a small burn right at the rim, and a strange sort of throbbing somewhere inside. Something pulsating. Castiel wasn't sure what it was, or how he would describe what he felt. All he knew was that a small part of him was curious about it.

As if he could read his mind, Dean straightened up, and pulled his hips flush against Castiel's.

Removing one of his hands from his hips, Dean let it wander over the dip of his hip bones to his thigh. He kept fucking into him slow, and on the third time he pulled out, he wrapped his hands around Castiel's dick.

Castiel gasped when Dean's fingers curled around him. While busying his mind with everything else, he'd nearly forgotten about his own pleasure in all of this.

Dean rubbed a thumb over the head of Castiel's cock, held his hand steady at the base, teasing before he began to stroke him, long and slow just how he liked it. "C'mon, yeah, there you go."

Castiel's eyes fluttered shut again as he focused on Dean's soft fingers and how they moved languidly along his shaft, tugging on him until he could feel his own pulse in his dick. "Ahh, Dean, please-"

"I got you." Dean jacked him for a moment before he curved his hand loosely around the hot, hard length. That way, once he began to thrust his hips again, Castiel's cock jerked forward into Dean's hand.

"D-Dean..." Castiel whined and slouched forward, struggling to keep up on all fours, _sort of_ beginning to enjoy this. Dean's silky smooth hand, wet with his own pre-come and slick with lube. His dick slid so hot and perfectly against Dean's palm, and the tip of Dean's cock kept nudging something inside him each time he retreated back and lunged forward. Something that sent dull throbs to his cock and throughout his body. It felt nice, sort of like with the fingers. Castiel wanted more, wanted to find that blissfulness again.

"Good boy, Cas," Dean praised him and picked up his pace just a little, tightening the grip around his cock. "Fuck, so good."

Castiel bent his head down against the mattress again. Dean was thrusting into him with a steady rhythm now, skin slapping against skin fast and hard, making the bed squeak and whine. Castiel wanted to join in, he wanted to come apart and whine and beg for Dean's cock too, but he didn't know if he could, afraid of how the words would sound coming out of his mouth.

Opening his eyes, Castiel bent his head inwards and put his chin to his chest to look at where his cock slipped between Dean's fingers. The head was red and swollen, glistening wet, beads of white dripping out and getting smeared all over Dean's fingers. Something pooled deep in his stomach again and Castiel wanted to grab Dean's hand and lick it off. He wanted to take his fingers, one by one and put his lips to them, peek his tongue out and lick around him.

"More," he said, voice dark and almost hungry. Surprised at himself, his cheeks flushed.

Dean chuckled. "Yeah, you like it?"

" _Please_ -"

"I knew you'd be a slut for my cock, Cas. Knew I'd drive you crazy," Dean said, a small growl rolling out with his words. He grunted, breaths coming out in forced puffs and his hand on Castiel's hip gripped tighter. "Wanna fuck your pretty ass all night baby, c'mon lemme hear how good you feel."

Castiel hissed. He felt frantic. Dean's cock was something special and it ignited sparks inside him. He burned, and he felt so, _so hot_ inside. His arms were shaky and his muscles pulled on his limbs but he stood up better on his knees to steady himself, so he could push back every time Dean buried himself inside him. He wanted to meet his hips, he wanted to hear their bodies come together. Wanted to be good for him, show him how much he loved this, how much he loved Dean.

"Dean, Dean," was all that came out of his lips. Then, tentative, "You feel so good."

"Got you, Cas. _Fuck-_ " Dean's breath was unsteady and fast. His thrusts were becoming erratic. Castiel knew he was getting close by the desperate, frustrated noises he was making.

Castiel closed his eyes and decided to let go and enjoy it. He couldn't see Dean's face anyway, and he felt his own body getting hotter, his balls tightening and his heart was beating like a drum. He might as well be ridiculous, Dean _obviously_ liked those girls in the videos, so he might as well act like one of them. Perhaps making noises and saying dirty words made things better? It seemed like it, going by what Dean was saying. I wasn't like he had anything to lose, he wasn't a virgin anymore, and if Dean didn't want to keep him after this, then so be it.

So he whined and called for Dean how much he _needed it_ , how he _wanted it_ with breathy, whimpering little moans, not caring anymore how ridiculous he sounded or if anyone heard until he could feel the muscles in his buttocks and thighs tighten as his orgasm was building.

"Fuckin' made for my cock, Cas," Dean panted and started jerking him quickly, drawing faltering noises from Castiel's lips with each pull of his cock.

Then suddenly, Dean dropped his cock and his hands scrambled for his sharp hips instead, as if he was pulling at anything of Castiel he could reach, yanking him backwards selfishly and rough. Castiel let out a sad noise before he drove himself back, meeting Dean's hips greedily, grinding his hips in circles and taking all the pleasure he could get to numb out the slight burn and the shame he was afraid that he was going to drown in if he let it get to him.

Then. Finally. That tightening sensation that pooled in his stomach and the promise of bliss rounded the corner as pleasure overwhelmed his body.

"Dean, I- I'm–" Castiel's eyes shot open and he clenched his hands in the sheets, feeling every muscle in his body tense up as the heat that was boiling deep in his stomach ignited, making it a struggle just to breathe. "I think I'm, _ah_ , Dean!" he moaned out his name, shutting his eyes tightly again, his breathing getting heavier.

The words fell from his lips as he let go of absolutely everything he was holding on to, letting go of every doubt and worry and any tiny little hint of shame or guilt that was left in his system, and he let it all spill out when something exploded and tore inside of him, his cock pulsing in defeat as he came harder than he ever had before.

Dean was still fucking into him, but Castiel could feel his thighs shaking, and it didn't take more than a couple of seconds and halfhearted thrusts before he was coming too, spurting hard and hot, emptying himself into the condom, Castiel's ass still clamping down around him hard, squeezing Dean's cock at the feeling of his hips stuttering helplessly, milking him of every last drop.

Just like that, it was over. But for some part, Castiel felt like it had only just begun.

Relief flooded his veins like ice in the summer, melting his muscles as he sank lower and lower down against the mattress and his mind was a blank slate. He felt like he could've sunk right through the bed when Dean collapsed on top of him, his body and limbs heavy and relaxed against his back. Now that they were still, Castiel could really feel the sweat clinging to their bodies, mingling between his back and Dean's chest, his skin growing cool from the chilly air in the basement. Dean was panting in long, heavy breaths, his torso enveloping Castiel in a comfortable embrace as they lay there blissful, riding out the aftershocks together for a little while.

Eventually, Dean pulled himself out and rolled over to the side. He had a stupid grin on his lips and a look on his face that made Castiel's chest tingle with appreciation once their eyes finally met, he'd done something right for once and the way Dean was smiling made it all worth it.

"That was...," Dean started quietly and trailed off, eyes glued on his boyfriend as he searched for the right words to finish the sentence with while Castiel curled up next to him.

Castiel pulled his knees up to his chest and wrapped his arms around them, an ache in his body reminding him like a bolt out of the blue of the reality of what had just happened between them.

Dean seemed struck by it as well, his palm suddenly on the side of Castiel's face. "Not right," he added, with an impossible small voice, his eyebrows tight together.

It was all it took for Castiel to crumble in on himself and close his eyes as regret and shame came over him like a tidal wave. Not even the apologetic way Dean was looking at him could make him feel better, the walls were slowly but surely crashing down around him to reveal the ugly reality of it, and he felt so utterly, horribly exposed and vulnerable.

And stupid. He'd been _so stupid_.

"I'm so stupid," Dean concluded.

"I'm stupid. I'm sorry," Castiel squeaked and all the other things he wanted to tell Dean got caught in his throat.

"What?" Dean scooted closer, his hand still lingered on Castiel's cheek gently. "Don't be," he murmured and wrapped his arms around his shoulders so Castiel could be pulled in against his chest. Castiel stayed quiet, didn't make a single sound except for the strained breaths that billowed out of him like smoke from a chimney against Dean's sweaty, sticky shoulder.

"I'm sorry too." Dean admitted eventually.

"You are?" Castiel asked, disbelief dripping from his broken voice. He blinked his eyes, sure that Dean could tell from the way his eyelashes were fluttering against his shoulder like light, tickling butterfly wings, that he was trying not to cry, because Dean started stroking his back and kissed the crown of his head before he replied.

"Yeah," he mumbled. "Yeah, I am. Fuck, Cas, it was great – you were great - but I shouldn't have pressured you into that."

He wasn't wrong, but Castiel still said nothing.

" _Fuck_ I'm such a selfish idiot!" Dean spoke fast and before Castiel could protest, Dean pushed himself backwards and away from him, making Castiel's head drop from his shoulder without a warning.

The sound level in the basement shifted so quickly, together with Dean's mood, and curse words were flying against the roof, the noise coming from Dean's mouth shocked Castiel out of his miserable state and he scrambled for his shaky legs to follow after Dean who had left the bed and was stumbling around the room.

"Dean-"

"Fuck, fuck, I'm so fucking selfish!" Dean roared and threw the heels of his hands against his eyes and kicked a leg out at the couch.

Castiel hopped down from the bed and hurried towards him, hoping his trembling, aching legs would carry him the short way. Once he was next to Dean, Castiel reached for his arm to try to calm him down.

"It's ok-"

"No! Get away from me, it's better if you just stay the fuck away from me!" Dean threw his arm out in front of him and pushed Castiel away in frustration, muttering swears under his breath and rubbed his hands over his face. Castiel could have sworn that his eyes looked glassy, but Dean was never going to admit that.

"Dean, stop, calm down." Castiel tried, reaching for his boyfriend again. There were many things Castiel was scared of, but Dean wasn't one of them. "It wasn't that bad, I promise."

"Not _that_ bad," Dean repeated, a bitter laugh escaped from the back of his throat.

The sound cut like knives through Castiel's chest, but he took another step forward anyway, again grabbing Dean's wrist.

"You didn't wanna do this, Cas, I know you didn't because you've been rejecting me over and over. I pushed you into this, I screwed up–"

Oh god, Dean's voice was trembling dangerously much, and maybe Castiel had been wrong, maybe there was something he was afraid of when it came to Dean after all; seeing him vulnerable and sad. He never wanted to see Dean upset, it hurt him more than anything, Castiel only wanted that stupid boy to always have his wolfish, shiteating grin plastered on his lips. Seeing the boy he adored so much, emotional and unstable, ripped Castiel apart. He'd only tried to make Dean happy... How had he managed to mess it up? Was it all for nothing?

"Fuck!" Dean swore again, anger seeping into his voice. At least he hadn't pushed Castiel off his arm this time. "I screwed up, Cas. I practically raped you, _shit._ I never should have laid a hand on you in the first place..."

He needed to fix this, _now._ He couldn't lose Dean now, not now. Not after giving him what he'd wanted. Anger bubbled up in Castiel's chest. He'd _wanted_ this. Begged Dean, told him how good he felt.

"Dean, don't," Castiel spoke up loudly and cleared his throat. He laced his fingers with Dean's and pressed closer to him, so close that their toes and thighs were touching. "Don't say that. Look, I'm... I'm not content with how it happened, but I don't regret it either–"

"You should. You deserve better," Dean said, cutting him off.

"Perhaps circumstances could've been different. But you were good to me," Castiel finished with a shaky voice.

"What the hell do you mean good to you? I fucked you ruthless. It was your first time, Cas, don't ever say I was good to you. I mean, look at this place," he said with a scoff and wiped a hand over his face again. Defeat was painted in his features, green eyes glassy. "I should've taken care of you properly. I should have listened to you, waited for you until you were ready and then I would have made it good for you, at least cleaned up in here before, gone through it with you slowly and maybe I would've..."

Dean's trembling voice was all it took for Castiel to stumble forward into Dean's, slightly hesitating arms, and crash against his chest. He couldn't hold his sadness back anymore, breaking down in little pieces, tears slowly running down his flushed cheeks, embarrassment aching in his bones. Castiel wished Dean had been the kind of guy who could say he'd wait forever if he had to, but that wasn't the kind of guy he was, Castiel guessed, and he hadn't wanted to find out either. He only had himself to blame for that, really.

Dean just stood there while Castiel hugged him, holding on to him as if he was afraid that he was going to storm off and disappear. Eventually though, Dean folded his arms around Castiel's back and leaned his head against his.

"Why'd you let me do it, Cas?" Dean whispered, and Castiel could swear he felt something wet trickle down from the other's face.

The question made Castiel feel dizzy, thoughts spinning around in chaos inside his head, as if it wasn't already a mess in there. "I don't know," he settled for at last, wondering if maybe he had been wrong in blaming Dean for all of this. Dean had just been horny, and that was normal in relationships, it wasn't anything strange or bad with wanting to have sex, right? Maybe it had truly been his own fault? Believing he would be forgotten and abandoned if he didn't give it up for Dean?

Castiel shook his head. "I'm worried you're going to leave me for somebody else..." he mumbled and swallowed hard. "I wanted to make you happy."

Dean sighed and he rolled his head back and let out a small grunt. "See. I'm a jerk. I knew you'd think that," he confessed and stressed his bottom lip between his teeth.

Castiel looked up from his shoulder, eyebrows drawn together in confusion. "What do you mean?"

"Man, I just wanted to fuck you," Dean continued and Castiel couldn't believe that his heart wasn't breaking because Dean deserved to be walked out on, he deserved to be left alone in his ugly, cold basement. But still, he stayed, hands resting at the small of Dean's back, listening carefully to every word he was saying. "I was selfish, Cas. I've said so many stupid things. I went too far, and I fucked it up and now you're gonna leave my sorry ass aren't you?"

Castiel played with the thought of shrugging and letting Dean think he would go, but then he decided that he wasn't going to sink that low, so he shook his head and looked up at Dean with sad eyes, trying to force out a smile at him. "No. You hurt me, Dean. And you're not going to learn anything from that if I walk out on you. Then you might go off and do the same thing to somebody else. So I'm staying."

Dean was quiet, bewildered, and then he shrugged. "I don't deserve that."

Castiel shrugged as well. "No, you don't."

With a sigh, Dean moved a hand up to Castiel's forehead and pushed a strand of hair back from his face. "I'll make it up to you, I promise. Next time."

Castiel frowned. "Next time?"

"I'm just kidding," Dean said, his mouth struggling into an insecure smile.

"You're not exactly making this any easier you know."

"I know, I know. Too soon."

Still, they both chuckled.

Perhaps there was some truth to Dean's words. Maybe next time would be better. Maybe, then Dean would want to look at him, make him feel whole instead of hollow.

"Alright you, come here." Dean pulled Castiel out of his mind and up easily into his arms so he could wrap his legs around his waist, cradling around Dean as he carried them back over to the bed. Dean moved his lips over Castiel's, kissing him long and slow and careful, capturing his lips with his own delicately. A few minutes later, Castiel broke away and his eyes darted briefly to the wall on the other side of the room, avoiding Dean's eyes.

"What's up?"

"Dean perhaps we should... you know, take it slow... considering."

Dean nodded and looked away as well. "Fair enough. But uh... Cas, can I ask you something?"

"Of course?"

"Apart from the whole... not really ready thing.. Did you enjoy it?" Dean bit his lip, eyes now back on Castiel, waiting impatiently for his reply.

Castiel took his time, on purpose of course, letting Dean hurt for a few, very drawn out moments of silence before he tilted his head from side and side. Then he laughed, stilted and awkward and a little ashamed. "Yes."

"Really?" The sheer joy in Dean's voice sent sparks through Castiel's chest and his heart jumped.

"Yes. Not at first but... Like I said, you were good. I think we can make arrangements for future occasions when I feel ready. I liked the crescendo of it."

"The crescendo?" Dean laughed warmly and kissed his cheek, and slowly but surely the ache in Castiel's chest was overtaken by anticipation.

Perhaps they could both grow stronger from this, together.


End file.
